YYZ - SXM

$142 Find Cheap Flights from Toronto to Simpson Bay

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Toronto to Simpson Bay departing on 8/21. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Simpson Bay

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Simpson Bay, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Simpson Bay, as well as popular online travel agencies
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Flights Deals

Cheap Flights from Toronto to Simpson Bay (YYZ-SXM)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Toronto to Simpson Bay that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Toronto to Simpson Bay

Sat, Nov 1 - Sat, Nov 8
United Airlines Logo
3:45 pm - 3:57 pmYYZ-SXM
24h 12m2 stops
United Airlines Logo
2:51 pm - 4:02 pmSXM-YYZ
26h 11m1 stop
$292United Airlines
Find Deal
Tue, Nov 4 - Tue, Nov 11
WestJet Logo
9:30 am - 3:21 pmYYZ-SXM
4h 51mnonstop
WestJet Logo
4:20 pm - 8:43 pmSXM-YYZ
5h 23mnonstop
$347WestJet
Find Deal
Fri, Nov 14 - Sun, Nov 16
United Airlines Logo
7:40 pm - 1:50 pmYYZ-SXM
17h 10m1 stop
United Airlines Logo
2:20 pm - 11:59 pmSXM-YYZ
10h 39m1 stop
$348United Airlines
Find Deal
Tue, Sep 16 - Sun, Sep 21
 Logo
9:00 am - 11:26 amYYZ-SXM
26h 26m1 stop
 Logo
2:10 pm - 7:10 pmSXM-YYZ
5h 00mnonstop
Sun, Oct 5 - Sun, Oct 12
American Airlines Logo
5:59 pm - 3:15 pmYYZ-SXM
21h 16m2 stops
American Airlines Logo
2:40 pm - 11:59 pmSXM-YYZ
9h 19m1 stop
$370American Airlines
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Sun, Oct 5 - Sun, Oct 12
American Airlines Logo
5:59 pm - 1:37 pmYYZ-SXM
19h 38m2 stops
American Airlines Logo
4:24 pm - 2:59 pmSXM-YYZ
22h 35m2 stops
$374American Airlines
Find Deal
Sat, Nov 1 - Thu, Nov 6
Air Transat Logo
6:30 am - 11:15 amYYZ-SXM
4h 45mnonstop
Air Transat Logo
1:05 pm - 8:52 pmSXM-YYZ
8h 47m1 stop
$387Air Transat
Find Deal
Sat, Nov 22 - Sat, Nov 29
Air Transat Logo
6:30 am - 12:15 pmYYZ-SXM
4h 45mnonstop
Air Transat Logo
1:25 pm - 5:50 pmSXM-YYZ
5h 25mnonstop
$444Air Transat
Find Deal
Mon, Sep 29 - Wed, Oct 1
Delta Logo
6:15 am - 1:50 pmYYZ-SXM
7h 35m1 stop
Delta Logo
3:20 pm - 11:55 pmSXM-YYZ
8h 35m1 stop
$506Delta
Find Deal
Sat, Jan 10 - Sat, Jan 24
Delta Logo
9:45 am - 12:15 pmYYZ-SXM
25h 30m2 stops
Delta Logo
5:16 pm - 11:34 amSXM-YYZ
19h 18m2 stops
$507Delta
Find Deal
Expert advice

Expert advice for your flight from Toronto to Simpson Bay

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
WestJet

WestJet's Premium cabin offers extra legroom and priority boarding on narrowbody aircraft.


WestJet allows bidding on upgrades for Business or Premium seats before your flight.

Read more about WestJetby Stefanie Waldek
Air Transat

Air Transat's Club Class offers wider seats and more legroom than economy.


Air Transat provides in-flight entertainment on most flights, bring headphones with a 3.5mm plug.

Air Canada

Air Canada offers priority boarding for Premium Economy and elite status passengers.


Air Canada provides Wi-Fi on select flights, check availability five days before departure.

Read more about Air Canadaby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on WestJet and Air Canada

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
John Walton

John Walton

Expert on Air Transat

John Walton

John Walton

Independent aviation journalist John Walton took his first flight at eight weeks old and hasn’t stopped travelling since. A world-renowned expert in airlines and the passenger experience, he writes in depth on aviation, is a resident expert on travel in Japan and France, and offers a uniquely queer perspective on travelling the world.

Read more
Booking Insights

KAYAK's insights & trends for Toronto to Simpson Bay flights

Get data-powered insights and trends into flights from Toronto to Simpson Bay to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Toronto to Simpson Bay?

The average price of all round-trip flights from Toronto Pearson Intl Airport to Simpson Bay clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Simpson Bay on a Tuesday and more expensive on a Wednesday. On your return trip to Toronto, you should consider flying back on a Saturday, and avoid Mondays for better deals.

What is the cheapest month to fly from Toronto Pearson Intl Airport to Simpson Bay?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Toronto Pearson Intl Airport to Simpson Bay, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Toronto Pearson Intl Airport to Simpson Bay is September, where tickets cost $286 (return) on average. On the other hand, the most expensive months are February and December, where the average cost of round-trip tickets is $590 and $562 respectively.

Can I save money by flying with a layover from Toronto Pearson Intl Airport to Simpson Bay?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $536 on average.

How far in advance should I book a flight from Toronto Pearson Intl Airport to Simpson Bay?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Toronto Pearson Intl Airport to Simpson Bay, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Toronto Pearson Intl Airport to Simpson Bay, you should book around 3 weeks before departure, which saves you about 15% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$142
Best time to beat the crowds with an average 39% drop in price.
Most popular time to fly with an average 20% increase in price.
Flight from Toronto to Simpson Bay

When to book flights from Toronto to Simpson Bay

Are your dates flexible? Find out the best times to travel from Toronto to Simpson Bay based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Toronto to Simpson Bay flights

  • What is the cheapest flight from Toronto Pearson Intl Airport to Simpson Bay?

    In the last 3 days, the lowest price for a flight from Toronto Pearson Intl Airport to Simpson Bay was $142 for a one-way ticket and $292 for a round-trip.

  • Do I need a passport to fly between Toronto and Simpson Bay?

    A passport is required to fly from Toronto to Simpson Bay.

  • Which airlines offer Wi-Fi service onboard planes from Toronto to Simpson Bay?

    Only Air Canada offers inflight Wi-Fi service on the Toronto to Simpson Bay flight route.

  • Which aircraft models fly most regularly from Toronto to Simpson Bay?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Toronto to Simpson Bay flight route.

  • On which days can I fly direct from Toronto to Simpson Bay?

    You can catch a nonstop flight from Toronto to Simpson Bay on Thursday, and Sunday.

  • Which is the best airline for flights from Toronto to Simpson Bay, Delta or Air Transat?

    The two airlines most popular with KAYAK users for flights from Toronto to Simpson Bay are Delta and Air Transat. With an average price for the route of $609 and an overall rating of 8.0, Delta is the most popular choice. Air Transat is also a great choice for the route, with an average price of $557 and an overall rating of 7.7.

  • How does KAYAK find such low prices on flights from Toronto to Simpson Bay?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Toronto to Simpson Bay.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Toronto to Simpson Bay?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Simpson Bay from Toronto is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Toronto to Simpson Bay?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Simpson Bay with an airline and back to Toronto with another airline. Booking your flights between Toronto and SXM can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Toronto to Simpson Bay?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Simpson Bay from Toronto up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Toronto Pearson Intl Airport to Simpson Bay

  • Looking for a cheap flight? 25% of our users found flights on this route for $169 or less one-way and $437 or less round-trip.

Prefer to fly direct from Toronto to Simpson Bay?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Toronto Pearson Intl to Simpson Bay Princess Juliana.
Find which airlines fly direct from Toronto Pearson Intl Airport to Simpson Bay Princess Juliana Airport, which days they fly and book direct flights.

Direct departures

Toronto Pearson Intl to Simpson Bay Princess Juliana

Thursday

WestJet

WestJet

Sunday

WestJet

WestJet

See more direct flights

Direct returns

Simpson Bay Princess Juliana to Toronto Pearson Intl

Thursday

WestJet

WestJet

Sunday

WestJet

WestJet

See more direct flights

Reviews of the top 5 airlines serving from Toronto to Simpson Bay

 
See real verified KAYAK customer reviews for airlines flying from Toronto to Simpson Bay. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Toronto to Simpson Bay? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 7980 reviews
7.3Food
7.9Comfort
7.9Entertainment
8.2Boarding
8.5Crew
Airline reviews

From Atlanta to Savannah - flight connection was way to short (we weren't even late landing ) and flight was already boarding when we landed - we were told we were the last on board and so we had to gate check our bags. Once we got on the plane, there were at least seven open bag spots so that was unnecessary delay. There should be better communication between the gate agent and the crew.

6.0 GoodBrenda, Jul 2025SAV - ATL
Read more Delta reviews

From Atlanta to Savannah - flight connection was way to short (we weren't even late landing ) and flight was already boarding when we landed - we were told we were the last on board and so we had to gate check our bags. Once we got on the plane, there were at least seven open bag spots so that was unnecessary delay. There should be better communication between the gate agent and the crew.

The way BCN airport handled boarding was a huge improvement over our trip to Spain from JFK. Instead of gate-mosquitos edging in before their zone was called, in BCN they had clearly marked lines for Zones 1-8 and people just lined up correctly. The flight itself was uneventful. The meal (curried chicken and rice) was one of the better meals we've had on Delta. Entertainment options were plentiful, power chargers were available in Main Cabin, and seats were decent. Flight staff were very friendly and positive throughout the 8 hour flight.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

After I checked in, I realized we had no seat assignment. It said they would be assigned at the gate. This was really frustrating because I usually use a lounge before flights, but I couldn't because I had to be at the gate to ensure we got our seat assignments. The gate agent arrived an hour before the flight left. I was the first one up to ask about seat assignments. She told us to wait for names to be called. Dozens of other passengers were paged, but we were not. Finally, I asked my husband to ask. He went up and was also told to wait. About 10 minutes later, they called for boarding. We still had not been told our seats. We went back to the desk and they were in a panic, saying we actually weren't on that flight. Then they made an announcement telling the stand by passengers to not board (in case we needed their seats). It was so stressful and unprofessional. Finally they gave us our seats. I have no idea what happened and why the two desk agents seemed to have conflicting ideas about our seats, whether we were on that flight etc.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

Friendly crew, quick boarding. We even arrived a few minutes earlier than our original flight plan. No onboard screens, but it’s a relatively short flight so it’s not really an issue.

Inexpensive, got an exit row aisle aeat with no middle passenger, bought a great breakfast sandwich, flight comfortable & arrived ahead of schedule.

Very dissatisfied with the fact that I had upgraded to first class for the second part of my trip only to find out that the lounge was still not available to me, as well as not having any food or drink service on the flight due to weather, so I lost out more than what I paid for.

Delta cancelled my flight less than 24 hours before departure and provided no alternative options. Left me to fend for myself basically. Scrambled to book flight on another airline and paid a fortune to do so last minute.. Can’t wait to see how Delta deals with my refund.

Check in slow even though completed online check in, there was no bag drop available so had to query for 90mins as only 2 staff on desks.

Flying to a far away destination is a miracle in itself, so please take these with a grain of salt. The seats are a bit tired, and need a freshen up. The entertainment could be a bit newer, especially with all services available now. The food really is where we need help. But again, flying is a privilege, so all is good.

Not so much porter it's your site! Not good

They are a sister company with Air Transat and the two companies do not work well together. If you have any issues the two companies will blame each other and you will miss your flights. The help line does not help

Never book through a third party. Book through Air transats website. Terrible process to get help and many issues happen with them and sister companies because half the flights you book with them aren’t even through air transat.

The plane was pretty full, and we dis not have any includes meal for our 4h30 flight? And on-board entertainment wasn't available, there was no TV or plugging to charger your device on the plane. They told us to download an app if we wanted to watch movies but it never connected, that was a disappointment, the r we st was very good though and the crew were really nice!

Seats were very tight especially for first leg of trip.

Not necessarily a Transat issue but it took 2 hours to go through immigration. Tried to reach out to Transat for resolution but was unable to reach an agent.

The flight was excellent, once it started, however we were delayed two hours when the first plane’s engines wouldn’t start. They found another identical plane and transferred us and our luggage in under two hours and made up almost an hour in the air.

Really low cost trip for the huge amount I paid…o paid 550 dollars just for the trip, one way trip, plus 95 for 1 luggage’s and the second 135 dollars…no blanket, not headphones for entertainment, food was served after 3 hours and 2 hours after, breakfast was served Bad, low cost company for high prices

Flight was cancelled 3 hrs AFTER etd. Thetefore Missed connection from JFK to New Zealand . No accommodation provided… This cost ne aporox 1000 USD in extra expenses and turned whst should have been a 24 hr trip ftom Boston - New Zealand into a VERY expensive , late 70+ hr nightmare … Complete nonsense!!!

A cookie and a soda, packed like sardines, will never be a positive experience. Also, boarded a 5:30 flight at 7:45pm

Mechanical delay and no compensation. Missed connection as a result of their delay. Mediocre performance and service. Horrible airline currently with horrible culture.

They cancelled my flight and downgraded me to economy and only gave me $250 for the downgrade

I was late from Jacksonville, FL but the limited interaction I had with the Philly crew was great.

Not very good , the stewardess were unfriendly and they don't like to be bothered. Cos was a night flight and they need to sleep.

Uncomfortable seats and flight attendant was rude as she insisted on waking up my husband to ask him if he wanted a drink. When he said that he was sleeping, she replied “without an attitude “. He was seated at 8c

Fine. On time, cabin service was fine, bag arrived. All good. Flying into DCA so did not collide with any helicopters, which is also good. Horrid incident that could have and should have been prevented.

rushed onto the plane by inpatient staff just to sit on the taxiway just want to add, the flight out of Philadelphia and into Fort Worth Texas was terrible. canceled twice because of non-existent weather, and delayed.

The drinks selection could be improved some. I like the fact that I can pick my seat and get upgraded fairly ofter.

7 hour layover was a drag. Free internet on the long leg was great.

Staff were courteous and helpful. The only negative was the flight delays (which are usually unavoidable) and the high baggage price.

From vancouver go calgary nd vice vetsa fligjt was delayed

Absolutely terrible, from the customer service to boarding the plane. On the phone, there was some mishaps with getting in my correct date and they did not help me retrieve a refund or any assistance. I’m gonna be reporting to all my followers and family around the region of Los Angeles to New York.

It was good! Short flight and it was on time!

Could not fly out of Canada. Called airlines on Monday, July 14th. Tried to cancel the flight 7 days away, but they said I could not cancel and there would be no refund.

Arrival at Comox from, London,ON 6 hours later... No bueano

Generally good. However. The flight left 30 mins behind schedule with no reason given.

Flight delayed, missed my pick-up had to Uber, plus missed dinner and medication, so sad!

Nothing to like because my inbound flight was cancelled without notification by West Jet or third party, JustFly. I couldn’t take the inbound flight due to cancellation; therefore could not take the outbound flight back.

Flying in the Dreamliner is always comfortable. Though the food options for Air Canada aren't great.

Flight got delayed for no reason. And Air Canada was doing 3 boardings via the same gate. It was chaotic!

I n the Toronto airport I had trouble finding my zone. It was 47. I went from Zone 1 to the end of the line.didn't find it. Then saw my zone somewhat by accident over by where you first come in. Signs could be more helpful or more personnel directing people like me.

Wonderful airline. All staff were pleasant and helpful. What is sad is that it wasn’t grand gestures just everyday pleasantness and friendliness that are missing from the other airlines I have flown recently.

Friendly efficient crew, but plane had no way to charge phone. That is a near necessity with today’s travel where we carry out travel documents on our phones.

Orderly boarding. The flight to Montreal was difficult to get to on time, but had help from staffer.

Orlando to Canada, despite being close and an international flight, the plane was not at all comfortable. It felt like the chair was being pushed forward, in addition to not having a TV and having to choose from a tiny glass of drink, for example, water or soda. I couldn't have both. When I asked the flight attendant for an extra glass of water, she looked at me with an ugly face. This is ridiculous. They don't want to give water to passengers. I will never fly with this airline again in my life.

The checking of my carry-on was not the greatest idea. It was selected for a security check in Toronto and didn't make it to my connecting flight. Fortunately Air Canada delivers late luggage to Whistler so I got it at 2 A M.

The seating and lack of leg room. I paid extra for more leg room. The space for under seat storage was a joke.

Well managed flight comfortable. Wish they had back of seat screens

Everything you need to know for your flight from Toronto to Simpson Bay

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